Iridium complex luminescent material containing dibenzothiophene sulfone group and its application

A technology of iridium complexes and thiophene sulfone groups, which is applied in the field of organic electroluminescent materials to achieve the effect of improving electron injection and transport capabilities and improving luminescent properties

Active Publication Date: 2020-04-14
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still few reports of high-efficiency yellow phosphorescent iridium complexes, especially bipolar yellow phosphorescent iridium complexes containing both hole transport units and electron transport units.

Method used

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  • Iridium complex luminescent material containing dibenzothiophene sulfone group and its application
  • Iridium complex luminescent material containing dibenzothiophene sulfone group and its application
  • Iridium complex luminescent material containing dibenzothiophene sulfone group and its application

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Experimental program
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Effect test

Embodiment 1

[0032] Synthesis of 2-(pyridin-2-yl)-7-(9-n-butylcarbazol-3 base)dibenzothiophene sulfone:

[0033]

[0034] (1) Synthesis of dibenzothiophene sulfone:

[0035]

[0036] Add 3.7g (20.0mmol) of dibenzothiophene, 10mL of glacial acetic acid and 6mL of 30% hydrogen peroxide into a 50mL round bottom flask, heat to 90°C, react for 0.5h, then add 2mL of 30% hydrogen peroxide, and continue the reaction for 0.5h . Cool to room temperature, filter with suction, wash with plenty of water, and dry in vacuum. Chloroform was recrystallized to obtain 4.1 g of white solid with a yield of 96%. 1 H NMR (400MHz, CDCl 3 , TMS) δ (ppm): 7.96 (d, J = 8.6Hz, 2H), 7.65 (d, J = 9.8Hz, 2H), 7.39 ~ 7.33 (m, 4H).

[0037] (2) Synthesis of 2,7-dibromodibenzothiophene sulfone:

[0038]

[0039] Add 3.89g (18.0mmol) dibenzothiophene sulfone and 120mL concentrated sulfuric acid into the flask, and stir to dissolve it. Add 4.0 g of NBS in small portions, and react at room temperature for 1 hou...

Embodiment 2

[0047] Synthesis of 3-(pyridin-2-yl)-6-(9-n-butylcarbazol-3 base) dibenzothiophene sulfone:

[0048]

[0049] (1) Synthesis of 3,6-dibromodibenzothiophene:

[0050]

[0051] Add 9.2g (50.0mmol) dibenzothiophene and 100mL chloroform into a 250mL three-necked flask, add 7.7mL (150mmol) liquid bromine dropwise at 0-5°C, and react at room temperature for 40h. Add saturated NaHSO 3 The excess liquid bromine was removed by aqueous solution to obtain a pale yellow solid, which was washed with water and ethanol to a white solid. Vacuum drying afforded 11.5 g of white solid, yield 67%. 1 HNMR (400MHz, CDCl 3 , TMS) δ (ppm): 8.22 (s, 2H), 7.71~7.69 (d, J=8.4Hz, 2H), 7.58~7.56 (dd, J=10.4Hz, 2H).

[0052] (2) Synthesis of 3,6-dibromodibenzothiophene sulfone:

[0053]

[0054] 6.8g (20.0mmol) 3,6-dibromodibenzothiophene, 150mL glacial acetic acid and 120mL tetrahydrofuran, and 15mL H 2 o 2 Add it to a two-neck flask, heat to 120°C, and react for 6h. After cooling to room ...

Embodiment 3

[0062] Synthesis of iridium complexes Ir-1-Cz and Ir-2-Cz:

[0063]

[0064] (1) Bis(2-(pyridin-2-yl)-7-(9-n-butylcarbazol-3yl)dibenzothiophene sulfone-N,C 2 ) (picolinic acid) iridium (Ⅲ) [Ir-1-Cz] synthesis.

[0065] Add 386.1mg (0.75mmol) of 2-(pyridin-2-yl)-7-(9-n-butylcarbazol-3yl)dibenzothiophene sulfone, 45mL of ethylene glycol monoethyl ether and 15mL of water into a 100mL In the three-neck flask, add 120.1mgIrCl rapidly under the protection of argon 3 ·3H 2 O, 100 ℃ constant temperature reaction 20h. After cooling, a yellow solid was produced, which was filtered by suction, washed with water and a little ethanol successively, and dried in vacuum to obtain a yellow powder. The product was directly used in the next reaction without further separation and purification.

[0066] In a 50 mL three-necked flask, 285.7 mg (0.082 mmol) of the reaction product of the previous step, 47.5 mg of 2-pyridinecarboxylic acid, 102 mg of sodium carbonate and 35 mL of ethylene gl...

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Abstract

The invention discloses an iridium complex luminescent material containing a dibenzothiophene sulfone group and its application. The iridium complex uses a dibenzothiophene sulfone pyridine derivative as a ring metal ligand and picolinic acid as an auxiliary ligand ; Introduce a hole transport unit on the ring metal ligand to balance the electron and hole transport capabilities of the iridium complex. Doping the iridium complex into PVK and PBD to form a light-emitting layer to obtain a high-efficiency polymer yellow light device; using the iridium complex and FIrPic as a dopant in a mixing ratio, doping the polymer PVK and OXD ‑ In 7, the light-emitting layer is formed, and the principle of complementary colors is used to obtain a high-efficiency polymer white light device, which promotes the application of OLED in flat panel display and white light lighting.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an iridium complex luminescent material containing a dibenzothiophene sulfone group and an application thereof. Background technique [0002] Due to the advantages of low driving voltage, fast response speed, low energy consumption, wide viewing angle, and flexible display, white organic light-emitting devices (WOLED) are used as a new type of solid-state light source in flat panel display, liquid crystal display backlight and solid-state lighting. Aspects have a wide range of applications (Chem. Soc. Rev., 2011, 40, 3467; Adv. Mater., 2011, 23, 233; Adv. Mater., 2014, 26, 2459). After years of research, WOLED has achieved rapid development, and its luminous efficiency has exceeded 120lm·W -1 , far exceeding the luminous efficiency of traditional incandescent lamps (10~15lm·W -1 ), showing great application prospects (Nature, 2009, 459, 234). [0003] Among ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/00Y02B20/00
Inventor 梁爱辉罗明刘志谦王涵刘德旺
Owner JIANGXI NORMAL UNIV
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